Hotels with Pool & Resorts in Chester from NZ$158

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Check availability on Chester Hotels with Pool

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Chester hotels with a pool

Indoor pool, pool loungers
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.6 out of 10, Excellent, (1007)
"timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs "
United States
Orlando
The price is NZ$170
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Hotel & Suites Chester by IHG
Miscellaneous
The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
"Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY."
United States
Erek
The price is NZ$417
includes taxes & fees
31 Dec - 1 Jan 2026
The Dominion House Bed & Breakfast
BBQ/picnic Area
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1005)
"Room was clean and staff was great!"
United States
Annemarie
The price is NZ$158
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn by Hilton Middletown
Seasonal outdoor pool, pool umbrellas, pool loungers
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (33)
"We are having a great time at the hotel!!!"
United States
Ziwei
The price is NZ$593
includes taxes & fees
2 Jan - 3 Jan 2026
LEGOLAND Hotel NEW York
Seasonal outdoor pool
Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (598)
"Very clean and quiet "
United States
Jeanette
The price is NZ$192
includes taxes & fees
2 Jan - 3 Jan 2026
Days Inn by Wyndham Wurtsboro
Indoor pool
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
2.5 star property
Fishkill
8.4 out of 10, Very good, (1008)
"Very nice stay."
United States
Peter
The price is NZ$174
includes taxes & fees
24 Jan - 25 Jan 2026
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Seasonal outdoor pool
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1004)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is NZ$203
includes taxes & fees
15 Jan - 16 Jan 2026
Overlook Lodge at Bear Mountain
Indoor pool, open 8:30 AM to 9:30 PM, pool loungers
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1012)
"Clean room, friendly staff, good breakfast"
United States
Zuriber
The price is NZ$204
includes taxes & fees
11 Jan - 12 Jan 2026
DoubleTree by Hilton Hotel Nanuet
Indoor pool
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very good, (1004)
"Love it, everytime we come this is the place to stay"
United States
William
The price is NZ$196
includes taxes & fees
1 Jan - 2 Jan 2026
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Indoor pool
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.2 out of 10, Wonderful, (1003)
"Yes stay was pleasant "
United States
henry
The price is NZ$181
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Suites Fishkill near Interstate 84
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Homewood Suites by Hilton Mahwah

Homewood Suites by Hilton Mahwah

10/10 Excellent
"Wonderful stay. Feel’s very much like home."
Mofolasayo 2-night trip
Posted 14 hours ago
Homewood Suites by Hilton Mahwah

Frequently asked questions

What are some accommodation options with pools in Chester?
Holiday Inn Express Hotel & Suites Chester by IHG: Hotel located near LEGOLAND® New York. Features on-the-go, a pool and complimentary high-speed (wired) Internet access. DoubleTree by Hilton Hotel Nanuet: Offers a snack bar/deli, a pool and free self parking. Sonesta Simply Suites Nanuet: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Features daily, an indoor pool and complimentary high-speed (wired) Internet access. Crowne Plaza Suffern - Mahwah by IHG: Offers a full-service spa, a seasonal outdoor pool and a snack bar/deli. Hampton Inn & Suites Mahwah: Provides daily, a seasonal outdoor pool and complimentary high-speed (wired) Internet access.
What is there to see and do in Chester?
Make a point to visit attractions such as The Rock Sports Complex and Castle Fun Center. Discover sights such as Museum Village and Goosepond Mountain State Park during your stay. The restaurants and shopping are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Chester?
You may want to consider a place to stay that has an outdoor pool if you plan to visit Chester in the hottest months of July, August or June, when the average temp is 21°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temperature is 0°C.